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Synthesis of the tri-deuterated GS-441524 analog. Reagents and conditions: (i) iodine, DMF, rt, 12 h; (ii) triethylamine, Pd/C, D2, anhydrous THF, 60 °C, 1 h;(iii) BCl3, DCM, −40 °C, 1 h; (iv) 2,2-Dimethoxypropane, p-toluenesulfonic acid monohydrate, acetone,45 °C, 2 h; (v) TEMPO, iodobenzene diacetate, NaHCO3, acetonitrile/water, rt, 5 h; (vi) trimethylsilyldiazomethane, THF/methanol, rt, 1 h; (vii) NaBD4, anhydrous THF/deuterated methanol, rt, 1 h; (viii) HCl, THF, 40 °C, 12 h.
